Icon-o-clash 3: The "Real-World" Edition

Uber-Geek vs Reverse Speak!
Napoleon: A new watershed of catch-phrases and pop-culture-speak was unleashed when this movie became popular. Mr. Dynamite has mad skills on the dance floor, is loyal to his friends. and can draw a Liger. All very cool.
Yoda: Sure he looks like Kermit the Frog and Ernest Borgnine's love child. Sure he speaks in a convoluted grammar that only Jean Chrétien could follow. But his wisdom and recognizable image make him undeniably cool. And, he totally kicked tail in the prequels.
Criteria: Grandma leaves Napoleon and Kip alone again. Uncle Rico is unavailable, so she calls the "Dagobah Housesitting Service" Yoda shows up like Mary Poppins. "Eat all the steak, I did not, my young padawan. Feed the alpaca, you now must."

Slothful Oaf vs. Beatnik Sailor
Homer: If the measure of a cool icon is the commonality it creates amongst pop culture consumers, then Homer is very cool. I've been to parties where the entire conversation takes the form of Homer-speak quotations.
Gilligan: Cool for his hat, his way with the ladies, and his ability to fight off giant rubber spiders.
Criteria: Gilligan arrives in Springfield and mistakes Homer for the Skipper. Homer sees the potential in having a willing first mate to order around. Discuss.

Dora Antagonist vs.
Swiper: Perhaps the most misunderstood villain ever. How would you react if every time you showed up, everyone started yelling at you and assumed you were going to steal your stuff? Personally, I'd want to steal the monkey's bouncy ball and throw it into the volcano too.
Superman: Some may say that his massive power level and flawless character make the Big Blue Boy Scout boring. All I know is I can tell my daughter a bed time story called "Clark who came to Earth in a rocket ship". Not sure if a story called, "Logan who had his skeleton removed" or "Bruce who beats up people because his parents got shot" would have quite the same charm.
Criteria: Swiper has jumped out from behind some bushes and is hopping...very...slowly... toward Clark. Clark, of course assumes that the sneaky fox is going to swipe his glasses, thereby ruining his perfect disguise and exposing his secret identity. Discuss.

Male Role Model Battle!
Han Solo: I'm sorry, did I say earlier that Fonzie begat Lost's Sawyer? My mistake, please turn your attention to Exhibit B. Additional coolness stems from the fact that he has provided one of the easiest Hallowe'en costumes for years.
James Bond: As with Dr. Who, please assess coolness based on any and/or all depictions and incarnations (although the most popular Connery version is depicted above). Suave with the ladies, deadly in combat, and a great stable of villains all combine to make Bond cool.
Criteria: These two are pretty evenly matched and their appeal comes from a lot of the same elements (cool gadgets, lots of action, charming with women, etc.) so debate should be hot and heavy on all fronts.